In 1940,Journal of Organic Chemistry included an article by Burger, Alfred; Avakian, S.. Synthetic Route of C7H4BrNO4. The article was titled 《Some derivatives of homoanisic acid》. The information in the text is summarized as follows:
p-Homoanisic acid (I), m. 86-7°, is prepared in a yield of 53% according to Arndt and Eistert (C. A. 29, 3223.9) by treating 20 g. p-MeOC6H4COCHN2 in 100 cc. dioxane with 150 cc. concentrated NH4OH and 30 cc. 10% AgNO3 solution at 60-70°. The mixture is boiled for 2 h. and the filtered p-homoanisamide, m. 188-9°, is saponified with KOH and I is precipitated on acidification. When 16.6 g. I is added to 30 cc. HSO3Cl at -5°, the mixture kept below 0° for 1 h., then warmed to 40° and kept there for 5 min., 3-chlorosulfonylhomoanisic acid (II), m. 164-5°, crystallized from C6H6, is obtained in 80.6% yield. Reduction of II with Zn dust and H2SO4 gives 3-thio-p-homoanisic acid (III), m. 83-4°, in 83% yield. That chlorosulfonation has taken place in the 3-position is shown by its synthesis from 3-nitro-p-homoanisic acid (IV). IV, m. 132-3°, is prepared in 70% yield by saponification of 3-nitro-4-methoxybenzyl cyanide, m. 87-7.5°, obtained by interaction of MeO(O2N)C6H3CH2Cl and KCN in 45% yield, with 50% H2SO4 in AcOH. IV is also formed when 0.5 g. I is nitrated with 1 cc. concentrated HNO3 in 5 cc. AcOH at 0°. Reduction of IV in the presence of Raney Ni gives 3-aminohomoanisic acid (V), m. 110-11°, in 90% yield. Treatment of V with NaNO2 in H2SO4, at 0° gives homoisovanillic acid, m. 127-8°. Treatment of the diazo compound from 7.24 g. V with a solution prepared by dissolving 12.4 g. Na2S.9H2O and 1.3 g. powd. S in 12 cc. boiling H2O gives on acidification 3,3′-dithiohomoanisic acid, which on reduction with Zn dust in AcOH, gives III in 25% yield. Condensation of 1.24 g. III with 2.46 g. 2-nitro-3-bromobenzoic acid, m. 250-1°, prepared by oxidation of 2-nitro-3-bromotoluene with Cr2O3 in 70% yield, gives 2′-nitro-3′-carboxy-2-methoxydiphenyl sulfide-5-acetic acid (VI), m. 232-4° (decomposition), in 46% yield. Reduction of VI in NH4OH with Fe(OH)2 gives the 2′-amino derivative, m. 222-4°, in 66% yield. In the part of experimental materials, we found many familiar compounds, such as 3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4Synthetic Route of C7H4BrNO4)
3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Synthetic Route of C7H4BrNO4 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary